I just got finished doing this in my second town. It's actually pretty easy..majority were their birthdays.
Deirdre wants to be a Journalist though and Phoebe is the 5th of 6 siblings.
- - - Post Merge - - -
Almost forgot, Octavian is great at trivia.
Apple is the 3rd of 4 children. She also wants to be a movie star. :3
Cherry's special skill is waking up early (could've fooled me; I have to have my game off by 11am if I'm going to be at work on time, so I never catch her until afternoon/evening)
Chief's talents at speed-reading also warranted a mention
Yep! Its when you can get Villager pictures, by answering questions about them. An NPC will ask you questions about a villager in your town,if you get it right,you get their pics.